EP0413762A1 - Peptidanaloge und deren verwendung als haptene zum auslösen katalytischer antikörper - Google Patents
Peptidanaloge und deren verwendung als haptene zum auslösen katalytischer antikörperInfo
- Publication number
- EP0413762A1 EP0413762A1 EP89906570A EP89906570A EP0413762A1 EP 0413762 A1 EP0413762 A1 EP 0413762A1 EP 89906570 A EP89906570 A EP 89906570A EP 89906570 A EP89906570 A EP 89906570A EP 0413762 A1 EP0413762 A1 EP 0413762A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- same
- alkyl
- side chain
- alkoxy
- integer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 125
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- 150000002148 esters Chemical class 0.000 claims abstract description 44
- -1 phenoxy, cyclohexyl Chemical group 0.000 claims description 143
- 125000006239 protecting group Chemical group 0.000 claims description 139
- 125000001424 substituent group Chemical group 0.000 claims description 129
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 97
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- 125000003545 alkoxy group Chemical group 0.000 claims description 77
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- 239000001257 hydrogen Substances 0.000 claims description 76
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- 230000007704 transition Effects 0.000 claims description 54
- 125000005647 linker group Chemical group 0.000 claims description 53
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 49
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical group 0.000 claims description 47
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- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 46
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- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 14
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- ULJUQHFPHRXUHF-UHFFFAOYSA-N 2-[2-oxo-3-(phenylmethoxycarbonylamino)cyclobutyl]acetic acid Chemical compound O=C1C(CC(=O)O)CC1NC(=O)OCC1=CC=CC=C1 ULJUQHFPHRXUHF-UHFFFAOYSA-N 0.000 claims description 6
- VHQSWDUQXAKZSS-UHFFFAOYSA-N 3-oxo-2-(phenylmethoxycarbonylamino)cyclobutane-1-carboxylic acid Chemical compound OC(=O)C1CC(=O)C1NC(=O)OCC1=CC=CC=C1 VHQSWDUQXAKZSS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 5
- PHJSXTLIFDVXOW-UHFFFAOYSA-N 3-hydroxy-2-(phenylmethoxycarbonylamino)cyclobutane-1-carboxylic acid Chemical compound OC1CC(C(O)=O)C1NC(=O)OCC1=CC=CC=C1 PHJSXTLIFDVXOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 4
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- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- XZYSSLBQKFSHLA-JTQLQIEISA-N 2-[(3s)-2-oxo-3-(phenylmethoxycarbonylamino)azetidin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C[C@@H]1NC(=O)OCC1=CC=CC=C1 XZYSSLBQKFSHLA-JTQLQIEISA-N 0.000 claims description 3
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
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- UOTZZIQMAUZIPW-UHFFFAOYSA-N 2-[2-hydroxy-3-(phenylmethoxycarbonylamino)cyclobutyl]acetic acid Chemical compound OC1C(CC(O)=O)CC1NC(=O)OCC1=CC=CC=C1 UOTZZIQMAUZIPW-UHFFFAOYSA-N 0.000 claims description 2
- AASNCWWREFPIJO-DGLNKRQFSA-N 5-[[(2s)-2-amino-3-hydroxypropanoyl]amino]-3,3-difluoro-6-hydroxy-4-oxoheptanoic acid Chemical compound OC[C@H](N)C(=O)NC(C(O)C)C(=O)C(F)(F)CC(O)=O AASNCWWREFPIJO-DGLNKRQFSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 13
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- AMOFITWOFBUTPT-BFHBGLAWSA-N (2r)-2-[(2-amino-3-phenylpropyl)diazenyl]propanoic acid Chemical compound OC(=O)[C@@H](C)N=NCC(N)CC1=CC=CC=C1 AMOFITWOFBUTPT-BFHBGLAWSA-N 0.000 claims 1
- JWUZUHZIOBRTHW-UHFFFAOYSA-N 2-(3-amino-2-oxoazetidin-1-yl)-3-methylpentanoic acid Chemical compound CCC(C)C(C(O)=O)N1CC(N)C1=O JWUZUHZIOBRTHW-UHFFFAOYSA-N 0.000 claims 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims 1
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- 230000000707 stereoselective effect Effects 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- VNOYUJKHFWYWIR-FZEDXVDRSA-N succinyl-coa Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 VNOYUJKHFWYWIR-FZEDXVDRSA-N 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 238000006449 thioacetylation reaction Methods 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- CNHYKKNIIGEXAY-UHFFFAOYSA-N thiolan-2-imine Chemical compound N=C1CCCS1 CNHYKKNIIGEXAY-UHFFFAOYSA-N 0.000 description 1
- 238000007079 thiolysis reaction Methods 0.000 description 1
- 238000007280 thionation reaction Methods 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 229960002175 thyroglobulin Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 210000003954 umbilical cord Anatomy 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/74—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C311/06—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
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- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
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- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have further substituents on alkyl
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- C—CHEMISTRY; METALLURGY
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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- C—CHEMISTRY; METALLURGY
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/5537—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom the heteroring containing the structure -C(=O)-N-C(=O)- (both carbon atoms belong to the heteroring)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K16/00—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K16/00—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
- C07K16/08—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from viruses
- C07K16/10—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from viruses from RNA viruses
- C07K16/1036—Retroviridae, e.g. leukemia viruses
- C07K16/1045—Lentiviridae, e.g. HIV, FIV, SIV
- C07K16/1063—Lentiviridae, e.g. HIV, FIV, SIV env, e.g. gp41, gp110/120, gp160, V3, PND, CD4 binding site
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0002—Antibodies with enzymatic activity, e.g. abzymes
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/25—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving enzymes not classifiable in groups C12Q1/26 - C12Q1/66
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/577—Immunoassay; Biospecific binding assay; Materials therefor involving monoclonal antibodies binding reaction mechanisms characterised by the use of monoclonal antibodies; monoclonal antibodies per se are classified with their corresponding antigens
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
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- G01N2333/005—Assays involving biological materials from specific organisms or of a specific nature from viruses
- G01N2333/08—RNA viruses
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- G01N2333/96425—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue from mammals
- G01N2333/96427—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue from mammals in general
- G01N2333/9643—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue from mammals in general with EC number
- G01N2333/96472—Aspartic endopeptidases (3.4.23)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US19027188A | 1988-05-04 | 1988-05-04 | |
US190271 | 1988-05-04 | ||
PCT/US1989/001951 WO1989010961A1 (en) | 1988-05-04 | 1989-05-04 | Peptide analogs and their use as haptens to elicit catalytic antibodies |
Publications (3)
Publication Number | Publication Date |
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EP0413762A1 true EP0413762A1 (de) | 1991-02-27 |
EP0413762A4 EP0413762A4 (en) | 1992-01-15 |
EP0413762B1 EP0413762B1 (de) | 2000-07-12 |
Family
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Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP89906570A Expired - Lifetime EP0413762B1 (de) | 1988-05-04 | 1989-05-04 | Peptidanaloge und deren verwendung als haptene zum auslösen katalytischer antikörper |
EP89906520A Expired - Lifetime EP0436545B1 (de) | 1988-05-04 | 1989-05-04 | Heilungsverfahren unter verwendung katalytischer antikörper |
EP95111577A Expired - Lifetime EP0701818B1 (de) | 1988-05-04 | 1989-05-04 | Heilungsverfahren unter Verwendung katalytischer Antikörper |
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Application Number | Title | Priority Date | Filing Date |
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EP89906520A Expired - Lifetime EP0436545B1 (de) | 1988-05-04 | 1989-05-04 | Heilungsverfahren unter verwendung katalytischer antikörper |
EP95111577A Expired - Lifetime EP0701818B1 (de) | 1988-05-04 | 1989-05-04 | Heilungsverfahren unter Verwendung katalytischer Antikörper |
Country Status (9)
Country | Link |
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EP (3) | EP0413762B1 (de) |
JP (3) | JP2772088B2 (de) |
AT (3) | ATE194649T1 (de) |
AU (2) | AU643186B2 (de) |
CA (2) | CA1340485C (de) |
DE (3) | DE68925972T2 (de) |
IL (1) | IL90200A (de) |
WO (2) | WO1989010961A1 (de) |
ZA (1) | ZA893284B (de) |
Families Citing this family (50)
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US5229272A (en) * | 1989-04-25 | 1993-07-20 | Igen, Inc. | Catalytic antibody components |
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US5236836A (en) * | 1989-04-25 | 1993-08-17 | Igen, Inc. | Autoantibodies which enhance the rate of a chemical reaction |
US5599538A (en) * | 1989-04-25 | 1997-02-04 | Igen, Inc. | Autoantibodies which enhance the rate of a chemical reaction |
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US5658753A (en) * | 1989-04-25 | 1997-08-19 | Paul; Sudhir | Catalytic antibody components |
US6258360B1 (en) | 1989-05-04 | 2001-07-10 | Igen International, Inc. | Prodrugs activated by targeted catalytic proteins |
DE69025761T2 (de) * | 1989-06-08 | 1996-07-18 | Igen Inc | Verfahren zur erhöhung der rate der modifikation metastabiler bindungen |
WO1991012021A2 (en) * | 1990-02-13 | 1991-08-22 | Oxford Virology Plc | Therapeutic agents, and intermediates for the synthesis thereof |
EP0527809B1 (de) * | 1990-04-05 | 1995-08-16 | CREA, Roberto | "walk-through"-mutagenese |
WO1993006838A1 (en) * | 1991-10-02 | 1993-04-15 | The Scripps Research Institute | Molecules with antibody combining sites that catalyze glycosidic reactions |
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JP2002516634A (ja) * | 1997-06-18 | 2002-06-04 | ザ ロックフェラー ユニヴァーシティ | 敗血性ショックおよび実験的関節炎の治療において有用な、抗体およびペプチドの同定方法およびその使用 |
IT1293511B1 (it) * | 1997-07-30 | 1999-03-01 | Gentili Ist Spa | Anticorpi monoclonali catalitici ad attivita' proteasica per la lisi selettiva della componente proteica di placche e aggregati correlati |
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WO2005077984A1 (ja) * | 2004-02-13 | 2005-08-25 | Osaka Industrial Promotion Organization | 有機化合物の製造方法およびそれに用いる抗体 |
GB2418427A (en) | 2004-09-02 | 2006-03-29 | Univ Cambridge Tech | Ligands for G-protein coupled receptors |
JP4861019B2 (ja) * | 2006-01-31 | 2012-01-25 | 独立行政法人科学技術振興機構 | ヒトTNF−αに対する抗体酵素およびその利用 |
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WO2016081297A1 (en) | 2014-11-18 | 2016-05-26 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
EP3233869B1 (de) | 2014-12-19 | 2019-09-25 | Rempex Pharmaceuticals, Inc. | Vorrichtung und durchflussverfahren zur herstellung von borsäurederivaten |
US20180051041A1 (en) | 2015-03-17 | 2018-02-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
ES2894251T3 (es) | 2016-06-30 | 2022-02-14 | Qpex Biopharma Inc | Derivados de ácido borónico y usos terapéuticos de los mismos |
IL273551B2 (en) | 2017-10-11 | 2024-02-01 | Qpex Biopharma Inc | Boronic acid derivatives and their synthesis |
CN113307863B (zh) * | 2021-05-25 | 2022-12-16 | 华南农业大学 | 一种聚天冬氨酸及其盐类抗体的制备方法和应用 |
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EP0305870A2 (de) * | 1987-09-02 | 1989-03-08 | Igen, Incorporated | Herstellung von Immunonähe-Katalysatoren |
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US4196265A (en) | 1977-06-15 | 1980-04-01 | The Wistar Institute | Method of producing antibodies |
WO1985002414A1 (en) * | 1983-11-29 | 1985-06-06 | Igen, Inc. | Method of catalyzing chemical reactions |
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-
1989
- 1989-05-03 ZA ZA893284A patent/ZA893284B/xx unknown
- 1989-05-04 DE DE68925972T patent/DE68925972T2/de not_active Expired - Fee Related
- 1989-05-04 AU AU37393/89A patent/AU643186B2/en not_active Ceased
- 1989-05-04 EP EP89906570A patent/EP0413762B1/de not_active Expired - Lifetime
- 1989-05-04 AT AT89906570T patent/ATE194649T1/de not_active IP Right Cessation
- 1989-05-04 JP JP1506288A patent/JP2772088B2/ja not_active Expired - Fee Related
- 1989-05-04 EP EP89906520A patent/EP0436545B1/de not_active Expired - Lifetime
- 1989-05-04 AT AT95111577T patent/ATE246004T1/de not_active IP Right Cessation
- 1989-05-04 CA CA000598754A patent/CA1340485C/en not_active Expired - Fee Related
- 1989-05-04 AU AU37304/89A patent/AU638405B2/en not_active Ceased
- 1989-05-04 WO PCT/US1989/001951 patent/WO1989010961A1/en active IP Right Grant
- 1989-05-04 AT AT89906520T patent/ATE135235T1/de not_active IP Right Cessation
- 1989-05-04 CA CA000598697A patent/CA1341478C/en not_active Expired - Fee Related
- 1989-05-04 DE DE68929230T patent/DE68929230T2/de not_active Expired - Fee Related
- 1989-05-04 JP JP1505991A patent/JP2931609B2/ja not_active Expired - Fee Related
- 1989-05-04 IL IL90200A patent/IL90200A/xx not_active IP Right Cessation
- 1989-05-04 WO PCT/US1989/001950 patent/WO1989010754A1/en active IP Right Grant
- 1989-05-04 EP EP95111577A patent/EP0701818B1/de not_active Expired - Lifetime
- 1989-05-04 DE DE68929479T patent/DE68929479T2/de not_active Expired - Fee Related
-
1998
- 1998-07-27 JP JP10211311A patent/JPH11152232A/ja active Pending
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US4659567A (en) * | 1984-09-07 | 1987-04-21 | Scripps Clinic & Research Foundation | Molecules with antibody combining sites that bind to hydrolytic transition states |
EP0251093A2 (de) * | 1986-06-23 | 1988-01-07 | Igen, Inc. | Herstellung von Antikörperkatalysatoren |
US4792446A (en) * | 1986-06-23 | 1988-12-20 | Igen, Inc. | Production of antibody catalysts |
EP0260939A2 (de) * | 1986-09-17 | 1988-03-23 | Scripps Clinic And Research Foundation | Moleküle mit Bindungsstellen von Antikörpern, die katalytische Eigenschaften besitzen |
WO1988009380A1 (en) * | 1987-05-28 | 1988-12-01 | Scripps Clinic And Research Foundation | Antibody combining sites that exhibit stereoselective synthase activity, and methods using the same |
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CHEMICAL ABSTRACTS, vol. 99, no. 9, 29th August 1983, page 600, abstract no. 70436q, Columbus, Ohio, US; C.C. WEI et al.: "Desulfurization of penicillins", & SYNTHESIS 1983,(4), 287-8 * |
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See also references of WO8910961A1 * |
Also Published As
Publication number | Publication date |
---|---|
CA1341478C (en) | 2005-04-05 |
JPH03504130A (ja) | 1991-09-12 |
DE68929230T2 (de) | 2001-02-22 |
JPH11152232A (ja) | 1999-06-08 |
AU3739389A (en) | 1989-11-29 |
EP0701818A2 (de) | 1996-03-20 |
EP0701818B1 (de) | 2003-07-30 |
DE68929479D1 (de) | 2003-09-04 |
EP0701818A3 (de) | 1997-06-04 |
EP0436545B1 (de) | 1996-03-13 |
JP2931609B2 (ja) | 1999-08-09 |
ATE135235T1 (de) | 1996-03-15 |
WO1989010754A1 (en) | 1989-11-16 |
AU643186B2 (en) | 1993-11-11 |
AU638405B2 (en) | 1993-07-01 |
DE68929230D1 (de) | 2000-08-17 |
JPH05501948A (ja) | 1993-04-15 |
DE68925972T2 (de) | 1996-07-25 |
ATE194649T1 (de) | 2000-07-15 |
EP0413762A4 (en) | 1992-01-15 |
DE68929479T2 (de) | 2004-04-15 |
ATE246004T1 (de) | 2003-08-15 |
AU3730489A (en) | 1989-11-29 |
WO1989010961A1 (en) | 1989-11-16 |
DE68925972D1 (de) | 1996-04-18 |
EP0436545A1 (de) | 1991-07-17 |
EP0413762B1 (de) | 2000-07-12 |
ZA893284B (en) | 1990-03-28 |
JP2772088B2 (ja) | 1998-07-02 |
IL90200A (en) | 1997-04-15 |
CA1340485C (en) | 1999-04-06 |
EP0436545A4 (de) | 1991-05-30 |
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